Simple and effective multi-component one-pot aldol addition/protection reactions of b-ketoesters to a series of aldehydes in the presence Me3SiCl and i-Pr2EtN have been described. The analysis of the scope of the reaction revealed a dramatic dependence of the reactivity on the substrates used. Thus the effect of a catalytic amount of DMF and different reaction conditions was widely investigated. Further transformations of the aldol adducts were particularly useful to give valuable diols and compounds with quaternary stereocenters, while X-ray structural analysis gave also important stereochemical information about this challenging reaction.

Multi-component, regio-selective aldol addition of b-ketoesters to aldehydes: scope and applications

DI MOLA, ANTONIA;TEDESCO, Consiglia;PEDUTO, ANTONELLA;DE CAPRARIIS, Paolo;FILOSA, Rosanna;MASSA, Antonio
2011

Abstract

Simple and effective multi-component one-pot aldol addition/protection reactions of b-ketoesters to a series of aldehydes in the presence Me3SiCl and i-Pr2EtN have been described. The analysis of the scope of the reaction revealed a dramatic dependence of the reactivity on the substrates used. Thus the effect of a catalytic amount of DMF and different reaction conditions was widely investigated. Further transformations of the aldol adducts were particularly useful to give valuable diols and compounds with quaternary stereocenters, while X-ray structural analysis gave also important stereochemical information about this challenging reaction.
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Utilizza questo identificativo per citare o creare un link a questo documento: http://hdl.handle.net/11386/3093654
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